1-(phenylhydrazono)-propan-2-one | 5391-74-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(phenylhydrazono)-propan-2-one
• 英文别名: 1-(2-phenylhydrazono)propan-2-one；Methylglyoxal-ω-phenylhydrazon；methylglyoxal phenylhydrazone；1-(phenylhydrazinylidene)propan-2-one
• CAS: 5391-74-2
• 化学式: C₉H₁₀N₂O
• 分子量: 162.191
• InChiKey: PWELTGGNVDVIGR-UHFFFAOYSA-N

物化性质

• 熔点：
  151-152 °C
• 沸点：
  266.9±23.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2928000090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Pyruvic aldehyde 1-phenylhydrazone
CAS-No. : 5391-74-2
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Oral (Category 4)
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36/37 Wear suitable protective clothing and gloves.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C9H10N2O
Molecular Weight : 162,19 g/mol
Component Concentration
Pyruvic aldehyde 1-phenylhydrazone
CAS-No. 5391-74-2 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 1,669
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-(phenylhydrazono)-propan-2-one 在 NaOMe 作用下， 以 甲醇 、 乙醇 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Unexpected Rearrangement of Palladacycles Derived from 2-Oxopropionaldehyde Phenylhydrazones. Synthesis of Palladium Complexes Containing a Bianionic Tridentate C, N, O Ligand

  摘要：

  The synthesis of bidentate monoanionic C-N derivatives of 2-oxopropionaldehyde phenylhydrazones, compounds 3, [Pd(2-{NH-N=CH-C(O)Me}-3-RC6H3)Cl(PPh3)] is described. The structure of 3b (R = Me) was determined by X-ray diffraction. The bond distances and angles are similar to those reported for related metallacycles. The distance N(2)... O(1) (2.583(7) Angstrom) shows the existence of a strong intramolecular hydrogen bond between the NH and COCH3 groups. The C(9)-O(1) (1.224(9) Angstrom), C(8)-C(9) (1.46(1) Angstrom), C(8)-N(1) (1.307(8) Angstrom), and N1-N2 (1.325(7) Angstrom) bond lengths indicate that 3b exists mainly in the keto-hydrazo form. The action of NaMeO on 3 in MeOH afforded deep violet compounds which did not contain chlorine atoms. The analytical data, the infrared spectra, and the NMR studies, including H-1-H-1 COSY and NOESY experiments, showed that deprotonation of the N-H bond took place to give 4, [Pd(2-{N=N-CH=C(O)Me}-3-RC6H3)(PPh3)] by means of an unexpected hydrazo-azo tautomerization. The structure of 4c (R = Et) was determined by X-ray diffraction. The C(10)-O(1) (1.32(1) Angstrom) C(10)-C(9) (1.37(1) Angstrom), C(9)-N(2) (1.33(1) Angstrom) and N(1)-N(2) (1.25(1) Angstrom) bond lengths indicate that 4c exists mainly in the azo-enol form. The action of HCl (0.5 N) on the tridentate metallacycles 4 regenerated the bidentate derivatives 3, showing the reversibility of this process.

  DOI：

  10.1021/om970240w
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 1-(phenylhydrazono)-propan-2-one
  参考文献：
  名称：

  v. Richter; Muenzer, Chemische Berichte, 1884, vol. 17, p. 1927

  摘要：

  DOI：

文献信息

• [EN] PYRAZOLOSPIROKETONE ACETYL-C0A CARBOXYLASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PYRAZOLOSPIROCÉTONE ACÉTL-COA CARBOXYLASE
  申请人：PFIZER

  公开号：WO2009144554A1

  公开（公告）日：2009-12-03

  The invention provides compounds of Formula (1) or a pharmaceutically acceptable salt of said compound, wherein R1, R2, and R3 are as described herein; pharmaceutical compositions thereof; and the use thereof in treating diseases, conditions or disorders modulated by the inhibition of acetyl-CoA carboxylase enzyme(s) in an animal.

  本发明提供了式(1)的化合物或所述化合物的药用可接受盐，其中R1、R2和R3如本文所述；其药物组合物；以及用于治疗通过抑制动物中的乙酰辅酶A羧化酶酶活性来调节的疾病、病症或障碍的使用方法。
• A novel approach for synthesis of 3-amino-5-aryl-2,5-dihydropyridazines using onium salt as soluble support
  作者：Meng Gao、Cui Fen Lu、Gui Chun Yang、Zu Xing Chen

  DOI：10.1016/j.cclet.2010.12.055

  日期：2011.7

  it was presented an application of task specific onium salt as soluble support for the synthesis of 3-amino-5-aryl-2,5-dihydropyridazines. This soluble support is of wide applicability and combines advantages of solid phase synthesis without its limitations with those of solution phase chemistry. After a simple washing step, products were cleaved from the supports and obtained in good yields.

  在这项工作中，提出了一种任务特定的鎓盐作为3-氨基-5-芳基-2,5-二氢哒嗪合成的可溶性载体的应用。这种可溶性载体具有广泛的适用性，并且结合了固相合成的优点而不受溶液相化学的限制。在简单的洗涤步骤后，将产物从载体上裂解下来并以高收率获得。
• Synthesis of [1,2,4]Triazolo[4″,3″:1′,6′]Pyrimido[4′,5′:3,4]Pyridazino[1,6-D] [1,2,4]Triazine; A Novel Tetracyclic System
  作者：Ayla Hazrathoseyni、Seyed Mohammad Seyedi、Ali Shiri、Hossein Eshghi

  DOI：10.3184/174751915x14241706062908

  日期：2015.4

  with hydrazine hydrate to obtain the new fused bicyclic 4-aryl-5-hydrazinyl-3-(1-hydrazonoethyl)-1-phenyl-1,4-dihydropyrimido[4,5-c]pyridazines via the Dimroth rearrangement is reported. Further cyclisation was achieved by the treatment of latter compounds with triethyl orthoformate to afford several derivatives of a novel tetracyclic fused system [1,2,4] triazolo[4″,3″:1′,6′]pyrimido[4′,5′:3,4]pyridazino[1

  6-乙酰基-3-氨基-5-芳基-2-苯基-2,5-二氢哒嗪-4-甲腈与原甲酸三乙酯再与水合肼缩合反应得到新型稠合双环4-芳基-5-肼基-3-(1-hydrazonoethyl)-1-phenyl-1,4-dihydropyrimido[4,5-c] pyridazines 通过 Dimroth 重排被报道。通过用原甲酸三乙酯处理后面的化合物来实现进一步的环化，以提供新型四环稠合系统 [1,2,4] 三唑并 [4",3":1',6'] 嘧啶 [4',5] 的几种衍生物':3,4]哒嗪并[1,6-d][1,2,4]三嗪。
• Ruthenium(II) bipyridine complexes bearing new keto–enol azoimine ligands: Synthesis, structure, electrochemistry and DFT calculations
  作者：Mousa Al-Noaimi、Firas F. Awwadi、Ahmad Mansi、Obadah S. Abdel-Rahman、Ayman Hammoudeh、Ismail Warad

  DOI：10.1016/j.saa.2014.07.080

  日期：2015.1

  correlation (HMQC) spectroscopy)). The two complexes exhibit a quasi-reversible one electron Ru(II)/Ru(III) oxidation couple at 604 mV vs. ferrocene/ferrocenium (Cp2Fe(0/+)) couple along with one electron ligand reduction at -1010 mV. The crystal structure of complex 1 showed that the bidentate ligand L1 coordinates to Ru(II) by the azo- and imine-nitrogen donor atoms. The complex adopts a distorted

  合成了新型偶氮亚胺配体Ph-NH-N = C（COCH3）-NHPh（C≡CH）（H2L），并通过X射线晶体学确定了其分子结构。在乙醇中在RuCl3·3H2O存在下于回流温度下催化H2L末端乙炔的水合反应，得到酮（L1 = Ph-N = NC（COCH3）= N-Ph（COCH3）和烯醇（L2 = Ph-N通过加水的马尔科夫尼科夫= NC（COCH3）= N-PhC（OH）= CH2。两种具有通式的混合配体钌配合物，反式-[Ru（bpy）（Y）CL2]（1-2）（其中通过将等摩尔量的（H2L）和bpy配体逐步加入到无水乙醇中的RuCl3·3H2O中，可以得到Y = L1（1）和Y = L2（2），bpy为2.2'-联吡啶。元素分析和光谱（IR，UV-Vis和NMR（1D（1）H NMR，（13）C NMR，（DEPT-135），（DEPT-90），2D（1）H-（1）H和（13）C-（1）
• Potentiometric, equilibrium studies and thermodynamics of novel thiosemicarbazones and their bivalent transition metal(II) complexes
  作者：Abeer Taha Abd El-Karim、Ahmed A. El-Sherif

  DOI：10.1016/j.molliq.2016.04.005

  日期：2016.7

  ligands and their corresponding metal-ligand formation constants with Cu(II), Ni(II), Mn(II) and Co(II) ions were determined at 15 °C, 25 °C and 35 °C in 50% DMSO solution at I = 0.1 mol·dm− 3 NaNO3. The stability order of complexes with reference to the metal ions has been followed this order Cu(II) > Ni(II) > Co(II) > Mn(II) in concord with the Irving-Williams stability order. Also, chemical equilibrium

  新型硫代半咔唑的质子化常数，包括2-（1-（2-苯基-肼基）-丙烷-2-亚烷基）肼基-碳硫磺酰胺（TPHP）和N-甲基-2-（1-（2-（2-苯基-肼基）-丙烷）在15°C，25°C下测定-2-亚丙基）肼基碳硫磺酰胺（MTPHP）配体及其与Cu（II），Ni（II），Mn（II）和Co（II）离子的相应金属配体形成常数I  = 0.1 mol·dm − 3 NaNO 3的50％DMSO溶液中在摄氏35度和摄氏35度。配合物相对于金属离子的稳定性顺序遵循以下顺序：Cu（II）> Ni（II）> Co（II）> Mn（II），与Irving-Williams稳定性顺序一致。此外，化学平衡研究表明，由于硫代氨基脲部分的取代氨基中甲基的电子释放作用，硫代氨基脲（TPHP）中的氢被甲基取代导致酸度降低。溶液中不同物种的形态已作为pH的函数进行了评估。此外，研究了温度对硫代半脲配体的质子化及其M（II